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$162+ Cheap flights from Caribbean Islands to Oregon

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Oregon

Keep the following information in mind while searching for Caribbean Islands to Oregon flight deals. Data was last updated November 3, 2025.

Round-trip from

$397
(Southwest)

One-way from

$162
(Kiwi.com)
From Caribbean Islands to Oregon
Search Deals
One-way flight from Caribbean Islands to Oregon
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Find flight deals from Caribbean Islands to Oregon

Cheapest flights from Caribbean Islands to Oregon
Explore the most affordable flight options available from Caribbean Islands to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/22:05 pmSJU - PDX
2 stops12h 30mSouthwest
Tue 12/96:55 pmPDX - SJU
2 stops11h 30mSouthwest
Deal found 11/2$397
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2210:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Tue 1/611:01 pmPDX - SJU
1 stop14h 00mAmerican Airlines
Deal found 11/2$427
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:00 amSJU - PDX
1 stop19h 16mAmerican Airlines
Sat 1/33:02 pmPDX - SJU
1 stop9h 58mAmerican Airlines
Deal found 11/1$473
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/187:15 amSJU - PDX
1 stop20h 11mAmerican Airlines
Thu 12/410:15 pmPDX - SJU
1 stop19h 54mAmerican Airlines
Deal found 11/1$482
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:00 amSJU - PDX
1 stop22h 30mAmerican Airlines
Sat 1/33:02 pmPDX - SJU
1 stop9h 58mAmerican Airlines
Deal found 11/1$487
This eDestinos deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:55 amSJU - PDX
2 stops35h 48mMultiple Airlines
Fri 1/211:20 pmPDX - SJU
1 stop27h 14mMultiple Airlines
Deal found 11/3$492
This eDestinos deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:22 pmSJU - PDX
2 stops31h 48mMultiple Airlines
Tue 1/66:14 amPDX - SJU
2 stops29h 59mMultiple Airlines
Deal found 11/2$496
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Fri 1/23:02 pmPDX - SJU
1 stop9h 58mAmerican Airlines
Deal found 11/3$501
This Gotogate deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:05 pmMBJ - PDX
2 stops41h 10mAir Canada
Fri 11/283:15 pmPDX - MBJ
2 stops18h 55mAir Canada
Deal found 11/3$657
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/72:32 pmMBJ - PDX
1 stop10h 36mDelta
Fri 11/285:26 pmPDX - MBJ
2 stops18h 04mDelta
Deal found 11/3$659
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:45 pmGCM - PDX
2 stops26h 46mUnited Airlines
Wed 12/2410:52 pmPDX - GCM
1 stop14h 43mUnited Airlines
Deal found 11/2$674
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:22 pmMBJ - PDX
1 stop10h 56mAmerican Airlines
Fri 11/281:47 pmPDX - MBJ
1 stop20h 13mAmerican Airlines
Deal found 11/3$680

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Oregon that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Oregon that are best for you.

Fly from

Caribbean Islands

Fly to

Oregon

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 12/2

2:05 pm-10:35 pm

2 stops12h 30m

Portland

Tue 12/9

6:55 pm-10:25 am

2 stops11h 30m

$397

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 12/22

10:25 am-12:59 am

1 stop18h 34m

Portland

Tue 1/6

11:01 pm-5:01 pm

1 stop14h 00m

$427

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 11/18

7:15 am-7:49 pm

2 stops16h 34m

Portland

Thu 12/4

10:15 pm-10:09 pm

1 stop19h 54m

$482

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 11/22

6:00 am-12:30 am

1 stop22h 30m

Portland

Sat 1/3

3:02 pm-5:00 am

1 stop9h 58m

$487

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

Wed 2/25

1:09 am-2:48 pm

2 stops17h 39m

Portland

Mon 3/2

7:00 am-11:57 pm

2 stops12h 57m

$509

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 11/14

7:45 am-8:38 pm

2 stops16h 53m

Portland

Fri 11/14

11:59 pm-3:40 pm

1 stop11h 41m

$540

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 11/14

12:55 pm-9:23 pm

2 stops12h 28m

Portland

Fri 11/14

11:59 pm-5:52 pm

2 stops13h 53m

$540

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 12/19

1:30 am-11:00 am

1 stop13h 30m

Portland

Sat 1/3

3:02 pm-5:00 am

1 stop9h 58m

$542

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 12/24

10:25 am-12:59 am

1 stop18h 34m

Portland

Thu 1/1

12:49 am-11:22 pm

1 stop18h 33m

$542

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sat 2/28

8:00 am-10:39 pm

1 stop17h 39m

Portland

Tue 3/3

9:45 pm-3:15 pm

1 stop14h 30m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 57 results
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Best time to book a flight from Caribbean Islands to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Caribbean Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Oregon

What is the cheapest month to book a flight from Caribbean Islands to Oregon?

Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Oregon (average of $228). Flying from Caribbean Islands to Oregon in October is currently the most expensive (average of $488). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EPX to OR?

Find hourly flight availability from Caribbean Islands to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Caribbean Islands to Oregon by exploring options for tickets in the evening.

What is the cheapest day to fly from Caribbean Islands to Oregon?

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Oregon. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Caribbean Islands to Oregon flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oregon. Reviews last updated November 3, 2025.
Read reviews from past customers who have flown American Airlines from Caribbean Islands to Oregon. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,037 reviews

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,037 reviews
American Airlines
7.2
Good
11,037 reviews

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Caribbean Islands to Oregon?

    Airlines like Southwest, American Airlines, and United Airlines fly from Caribbean Islands to Oregon in about 12h 30m. The time it takes to get you to your destination can typically vary by up to 6h 04m. There are 3710 mi between Caribbean Islands and Oregon. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean Islands to Oregon one-way?

    The cheapest airlines for a one-way flight from Caribbean Islands to Oregon are Southwest ($198), United Airlines ($198), and Frontier ($209).

  • Can I find deals for flights from Caribbean Islands to Oregon that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands to Oregon?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Oregon.

  • Can I find deals for business class flights from Caribbean Islands to Oregon?

    Yes. Cheapflights offers flight deals from Caribbean Islands to Oregon by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Caribbean Islands to Oregon?

    Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Oregon (average of $228). Flying from Caribbean Islands to Oregon in October is currently the most expensive (average of $488). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Caribbean Islands to Oregon

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Top 4 airlines flying from Caribbean Islands to Oregon

Discover the top 4 airlines that operate flights from Caribbean Islands to Oregon. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$522FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$497FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$573FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

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